Madeleine Dore | Redefining What it Means to be Productive

Srini Rao: Madeleine. Welcome to the unmistakable creative. Thanks so much for taking the time to join us. It's

Madeleine Dore: such a treat to be joining

Srini Rao: you. It is my pleasure to have you here. I just found out from talking to you that you have been a long time listener. You have an amazing book out called I Didn't Do the Thing Today, which is probably one of the most contrarian views on productivity I've come across in all the time I've been doing this in a world that is absolutely obsessed with productivity.

But before we get into all that I wanted to start by asking you, what did your parents do for work and how did that end up shaping what you've ended up doing with your life and career?

Madeleine Dore: I have always appreciated this question that you've asked because I think it's such a beautiful way to explore how it's not necessarily what you do, but the way that you do it.

And I think that this particular approach that my parents have had to their careers has influenced me in a way that I didn't really appreciate until. recent years. And in particular, my mom she grew up in public housing and she was the first in her family to go to university. And she studied primary education there and then went on to become a kindergarten teacher.

And from there, she then went and became a teacher at a community college to teach kindergarten teaching and slowly worked her way up different leadership positions. And in order to do that, she actually had to move around a lot. So she'd have to follow the opportunities. To different regional towns in Australia and eventually Melbourne, and then went on to become a CEO at a particular community college.

And she would commute while we, the family lived in Melbourne. And so she held these different positions over time and has even held positions in the Pacific. So that's an even longer commute. And I think what that really helped that trajectory from kindergarten teacher to CEO. really showed me that there are possibilities and it's important to live a life of possibility and to go after opportunities.

And I think many things enabled that in terms of being able to pursue particular possibilities. But the bedrock was my dad's willingness to support my mom's career and to follow her to, to these different towns without question and for her to pursue this career. And I think what I suppose turning to my dad, what made that possible is that he worked as an electrician so a tradie, and it meant that his career was portable and I can now see as someone who has created a life where I can work as a writer, a freelancer and really make the most of that.

The free part of freelancing in terms of working from different cities and settling in different countries for months at a time and having that portable life, I think was a huge influence. And so while my mom has definitely inspired me in terms of being a primary earner in the family and show me what's possible in terms of aspirations and opportunities, I think that with my dad, what I've come to appreciate even more recently is that as a tradie but also maybe he's able to be a master craftsperson in many ways and can create anything.

There's very much the possibility in that too, in a very tangible way, creating something from nothing. And I think we can overlook that type of creativity. Often when we speak about creativity might be about art or design or film or music, but there's a real tangible creativity that trade people have.

And there's so much to learn from people who are solving problems every day with ordinary materials with their own hands. And that's very creative as well. So I think the combination of my parents has really shown the beauty of flexibility and of how to be creative and pursue different possibilities.

Yeah.

Srini Rao: I assume when you say tradie, that's the Australian term for a blue collar worker, just out of curiosity. Is that, would that be correct? What we would call blue collar labor. Yeah. Okay. So what I wonder is when you have a dad who's an electrician and a mom who is an educator, what was the narrative about education in your household?

And also in the Australian culture in general, what is the narrative about education? Because I know that you guys, for the most part, like everybody does a gap year before they start university. Whereas here you're just put on this conveyor belt from the time you're 18 years old. without ever stopping to question why you're doing what you're doing, whether it's actually going to be a fit for you and whether it's going to lead to the satisfaction you think it will.

Madeleine Dore: Yeah. I think the first part of that question in terms of having a parent, one's an electrician, one's an educator. I think what's been instilled is this idea of lifelong learning. I think that's the thread and that we can learn from so many different things in our lives.

And especially with college a community college, it's really seeing that it's not necessarily being on a conveyor belt of academia or prestige. It's about pursuing whatever it is that you want to learn. And there's accessible pathways to that. Learning doesn't have to cost anything.

Learning can be learning from other people, learning can be an apprenticeship learning can be from trying and creating and failing and trying again. I think that's something that comes from both. And then in terms of it's difficult to speak to a whole Australian view, but it's interesting what you note about the gap year, and I think that certainly not everyone takes a gap year and I people go on to pursue many different pathways, but maybe I've thought about it.

Myself, and perhaps it's because we are an island in the middle of the ocean that's far away. Perhaps there is more of an impetus to if we travel, I know certainly for myself I don't want to just in terms of consciously being aware of, okay if we're traveling so far, then make the most of it in terms of really setting aside some time rather than rushing through.

through places and having, if we're going that and taking that 24 hour flight even recovering from the jet lag might be worth settling somewhere for a year. Yeah.

Srini Rao: It's funny because I have noticed that probably the people that I have met most when I have traveled to all the different countries I've traveled to are Australians.

Like every youth hostel I've stayed in has had an abundance of Australians. And I remember I was at a youth hostel in Amsterdam, these two Australian guys, I think they were construction workers, like nine o'clock in the morning, like, all right, let's go smoke a joint and drink a beer. And I was like, it's nine o'clock in the morning.

They're like, we're on holiday, man. Okay, this is how the Australians take vacations. Good to know.

Madeleine Dore: Certainly not all. I haven't had the nine o'clock beer.

Srini Rao: Yeah. Okay. Good to know. Keep in mind, that was what I was in my early twenties. I think I wouldn't find that to be the case now, but in Australia, when it comes to education, do you have this structure of like elite universities and top notch schools, like we do here in the United States where you have the Ivy league.

Is there anything that's the equivalent of that in Australia? And then how does that. shape people's career paths and motivation and desires when they're younger.

Madeleine Dore: I suppose we don't really have a Ivy league equivalent. And perhaps because I suppose the student loan system operates quite differently in, in terms of it.

It's there's, there seems to be there's not the same pressure of it's through the government the loan and so there you can pay that back through your tax over years, decades and so on. And so perhaps it's not the same I suppose debt is the way that it is a debt, but it's perhaps there's a little bit more flexibility or freedom in terms of pursuits.

And there's, again, not someone who's embedded in the world of academia. I'm sure that there's always a level of prestige that when you're in a certain world, you're more aware of the hierarchy of things. And again, it's not something I can really speak to. directly, but I think that even seeing there's not really, when I say community college that my mum taught at and then eventually was in leadership roles, there's not really an equivalent, I don't think.

It's, so it's skills that adults can develop and so it's not necessarily something that you go to, you might go to it even during high school, instead of finishing high school, you might go to what's called a TAFE or community college or you might be an adult learner and go and reskill in something.

And yeah, it's interesting to reflect on because I think that I've always seen that there's a wealth of opportunities and it's really about, I don't know whether it's my direct upbringing or whether it's a specific Australian thing. But that there is, it's not necessarily a pressure to get on a certain track.

It's about really discovering what it is that you wish to do. And then this can be different pathways there, but again, that could be. a certain luxury of mine in terms of being influenced by. Someone who's pursued different possibilities for themselves.

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Srini Rao: Hey, listener Miles here from Acast. Thanks for listening to one of our shows. Here's a question for you. Have you ever thought about starting your own podcast? We believe that everybody

Madeleine Dore: has a story to tell, so whatever

Srini Rao: you love talking about, we know there are listeners out there who will love to hear it.

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Get started with a three month free trial of our paid plan using the promo code. Start just visit go. acast. com slash start a cast. We're the home of podcasting. As I'm listening to you, I just, I can't help, but think that. There's no way an American person could have written this book that only an Australian would have written a book with this very contrarian view on productivity. With that in mind curious, what is the narrative about work culture in Australia?

Because I think that the the sense I get is. A lot of countries other than the United States, people live work to live. Whereas in the United States, we basically live to work, like work dominates our lives here in the United States. It's such a big part of our lives that from the time you're in college, you're starting to think about what you're going to do for work.

And we asked kids when they barely have been on the planet for very long, what do you want to do when you grow up? It's wait, this kid hardly knows themselves and you're asking them what they want to do for the rest of their lives when they've only lived a fraction of it.

Madeleine Dore: That's really interesting because I see that and I, I can see that would, there would certainly be people everywhere. I think that is becoming quite a contagious thought, not only contagious, but in, in some parts of the world, very necessary to work, to survive. And so it's so complex to unpack and I suppose I can only really speak to this idea that I chose similar to you to speak directly to creative people.

Not necessarily to find out a perfect or comprehensive portrait of an Australian approach to work, but rather an, a creative approach to work. And so I did interview people from Australia and the U S and I suppose it's when you're looking at this particular subset of people who are choosing to, to live a life that is different it's difficult for me to speak to a standard attitude with any authority. So I'm not going to pretend to. So I think it's more that I was curious, something inside of me wanted to know that it's possible to live a different sort of life. And so I sought out people I thought who were doing that. And that became the inspiration and to see that it is possible to step outside.

Yeah, I guess the confines of what a productive day or the hamster wheel and that's complex and difficult.

Srini Rao: Did you notice any differences in the way that people viewed productivity when you talk to people in different cultures? What was the sort of narrative that people had about productivity?

Because. Like I think I read this book and part of it made me cringe because I'm like, wow, I'm basically everything that she's saying is wrong. And at the same time, I find myself agreeing with you and nodding. And I was like, yep, that's wrong with me too. I do this too. I'm obsessed with the productivity, but and we'll get into the book here in just a second.

But I, that, that's something that I was really curious about. I was like, you're talking to people from different cultures, like how particularly creative people, how did it differ?

Madeleine Dore: I feel like I have to caveat and say that this book is built from a where I was speaking to people who I had direct access to.

So it's again, by no means comprehensive, nor is it rigorous in its study anthropologically. So there's no way that I could comment on something so vast and complex as culture. Again, I was just speaking to who I could, when I could it was a labor of love. So it was done when I had the time and curiosity picked up and put down.

And it really stemmed from all these stumbles that I felt within myself. So anything that you might come across in the book as being wrong with you, which I want to put in air quotations. It's because I was having that very stumble I was coming up against my own perfectionism as well, or my own obsession with productivity or my own sort of attachment to what I do being the definition of who I am.

And so I think that these are all I was speaking and taking these really tricky some might frame it

,

as internalized capitalism. Taking that to people who I thought might have the answers. As a way to solve it within myself. And again I think just to underline that a lot of these things were very personal questions that I had and then put to individuals.

And even though we can find the universal in individuals. By no means can I yeah, sum up neatly, unfortunately, Srini, any kind of broader commentary. It was more just looking for answers in little corners. And so the people I spoke to in different countries which again, primarily Australia and the US, it was very much to look for what kind of gems that person had very much as you do so beautifully as well.

Srini Rao: Oh, yeah. I appreciate you caveating everything with that because I think there's so many people who have a tendency to position themselves as authorities and experts with nothing to back it up. But the fact that you're. Openly saying that I think just means a lot to me. You open the book by saying that when we conflate productivity with worthiness, what we do is never enough.

We can always do more and there's always more to do. And I I just think about how I'm sitting at the end of the day, making a to do list thinking, yeah, there is always more to do. Is there any way to decouple this idea of conflating productivity with worthiness? Like, how do we not tie our worthiness to our productivity?

I guess is what I'm saying. Yeah, I

Madeleine Dore: think that's the big wrestle, I think, because it is this hamster wheel. And in, in many ways there's nothing wrong with being productive either. There's those days where we do tick off everything on our to do list. They have this amazing shimmer to them and it feels good.

And I think in part, we're chasing that feeling that high that being productive and that meaning sometimes that being productive can bring, like we want to do the things that are important to us. And so it's not necessarily productivity. That's the problem. It's just that it's the wrong goal.

And in terms of we really narrow how we view productivity. We see it as this consistent linear. Progress is this upward trajectory that has to come with being productive. But actually productivity doesn't necessarily have to look like that. And instead of pursuing that very narrow version and attaching a sense of self worth to that version which is essentially more, so there's never enough.

We can reframe it and see, I, as I speak about taking a more creative lens to our days and to our work and to our lives and to our connection, because a more creative lens will allow us to, to acknowledge that there's an ebb and a flow to things. I think we, we know intuitively maybe that there's.

An ebb and flow to our energy and our attention and even the productive days, like that beautiful shimmering productive day that we might have is often followed by a lower energy day where we do need to recoup. And so there tends to be a kind of ebb and flow to it. And so a creative approach means that we can really broaden things and we can broaden it so that we don't have to feel deflated on the days that don't go to plan or there's a distraction or we don't get enough done because we can see that it's part of a different kind of cycle and we can see that those days have value too.

And it might be that that day was more about thinking or it was more about connecting than necessarily the doing part of it. And so I think it's really important to see it as part of a cycle rather than just fixating on one part of it. Because yeah, as humans, we're we're complex and we're inconsistent.

And I think that our work patterns reflect that, but we forget, and we're trying to squeeze ourselves into these boxes that, that are really hard to maintain and to achieve essentially.

Srini Rao: Yeah you talk about routines and you say the ideal routine we draft for ourselves in which productivity is optimized, distractions are minimized, and our output is at a maximum, and then the messy everyday reality of our days as they unfold, rarely is the aspirational ideal achieved.

On most days, we're just adjusting, tumbling, and rebuilding, and then you actually go on to say the aspirational routine to which we're pinning our hopes of being better is more like a mirage. In which, although we strive for it, we rarely reach what it promises. And the reason for this is the variance inherent in our days, in our energy, in our interests, in our interactions, in our everyday chaos, our perfectly ordered life will always remain outside the imperfect reality of the daily lives.

And you actually say that creating the ideal routine rather ironically can be the very thing that lands us into a rut. And as I mentioned to you before we hit record today, like my routine got thrown off simply because we were out of food at the house and I was like, damn it, everybody ate everything and now my day is shot to shit.

I needed to be here an hour earlier so I could read before I talked to you and I didn't get to do that yet. But I think the real thing that struck me when I read your book was that idea of a routine becoming a rut. And the reason that stood out to me so much was because during COVID, I got into a standard routine every day.

It was the same thing. I would sit down in my basement at my house in Boulder and I would just read and I would write for hours on end. And I remember when my second roommate was moving out to go to Chile for the summer. He said, Trini, he was like, you need to move out. He said, cause I know you well enough to know that if you don't move out of here.

You're going to just sit in this basement, reading and writing for the rest of the summer. And I ended up actually going down to South America with him, but I didn't even recognize I was in a rut until after I pulled the plug on it, but I realized that the routine had become a rut. So talk to me about how, one, we can make sure our routines don't become ruts and two, how we don't lose our shit when things don't go according to plan, even though because a lot of creatives I think are really weird like this, they're creatures of habit to a fault.

And when things don't go as planned, it drives them insane.

Madeleine Dore: Yeah. Which is interesting because isn't that like where a lot of epiphanies and ideas come from is the unexpected surprise and the things that don't go to plan. It's the definition of creativity is that's that landing on something new that new combination.

And so it's funny that we resist the very thing that is what we're searching for. It the, I guess that's yeah. And that relates back to this idea of a routine meeting, a rutt is that again, just like productivity, there's nothing inherently wrong with being productive. There's nothing inherently wrong with a routine.

A routine can be really grounding. It can be something that we can really rely on, especially during times of uncertainty. It can be the thing that, that can be paramount to our mental health. But I think what can be tricky is the aspirational side of it. So it's not so much the routine, but this idea that we should have a particular type of routine and that we should stick to it every day perfectly.

So it's more the the side effects of perfectionism and comparison that actually can make a routine I guess something that's, it's, yeah it's almost this hamster wheel again of chasing something that you, or a mirage, as I say, because you don't ever quite arrive there.

And so by very nature of never arriving there, you're postponing your life. A lot of people as soon as I get a routine, I will dot dot. And just accepting that maybe you won't arrive at the perfect routine or you'll never be quite perfectly consistent. You can still actually make the most of every day though, that doesn't have to be there.

That's my warning about routine or aspirational ones, but in terms of, again, this idea of meeting a rut or this idea of even aspiring after it, sometimes it strikes me as, as odd because. What is a routine? It, by definition it's a pattern, it's stagnant, it's the same. And we want our days to look like that, which is then almost a groundhog day.

If our, if we stuck to the perfect routine, we'd have the same day over and over again. And isn't it that we want our lives to have variance and interest and depth and learnings. And that comes from things. having that variance. And so the rut is very much, I think it's it might be a common experience to land in one without realizing because here we are pursuing optimized routines and optimized productivity and then getting, say we got there.

Then we just have the same day over and over again and not realize that we're actually stuck in something. And so that's where they meet each other. They meet each other simply through the definition of the two words, really, because a rut is being stuck in a wedge in a groove.

And so you might have a routine for a while that is a groove, but then you get stuck in that very groove. But interestingly, I think that with a rut, whether it's because we landed there without even realizing or whether sometimes we get stuck in a rut because of something external happening to us heartbreak or loss or a major change.

You can get stuck there for a while and it can be difficult because there's the culture might say push yourself out of the rut. We idolize routines. Yet we demonize being stuck in a rut it's like being told to get over it. But often if we force that, we'll just become further wedged.

And so it's really about slowly retooling yourself to be able to get out of that rut. And interestingly where this all comes full circle is that sometimes it's then about turning back to your day and finding small good things that you can turn to during that time of a rut, be it exercise or be it having meditation or whether it some kind of way to that makes you feel like you're bringing either joy or health or vitality back. And those very things can start to build up and look like a routine again. And so then it becomes this interesting cycle, I think. But again, I think the most important part of it, like all of this is to see that each part has its own value, whether it's you're in that routine, whether you're in that rut.

And really the rut has so much value because it's showing you that something's not working anymore. It's showing you that you crave a change. And that maybe it's alerting you to the fact that you are becoming too complacent and it's time for something new and you might not know yet what that is.

And so it feels like you're stuck, but maybe be patient with that rather than trying to cover over it. I think that's the hardest part is the patience. When you mentioned perfectionism, I couldn't help but thinking about the role that social media plays in all of this. And I I didn't even watch it, but I remember Ryan Holiday puts up a video on Instagram just a few days ago where it's this is the morning routine.

Srini Rao: And I couldn't help but think, okay, everybody's probably okay, I need to be like that or. My friend Benjamin Hardy, I'm sure you've come across this article, the eight things that everybody should do before 8am. And I remember talking to him, I was like, Ben, if somebody didn't get any sleep, there's nothing on your list they should do.

They should get some damn sleep. And I think that's, I wonder, like in your opinion, what role does the media we consume and social media play in our aspirational routines that we create in our heads?

Madeleine Dore: I really loved your, that's a great counterpoint to have in the, in terms of that eight things before 8 AM.

I think that it really comes down to I think that it's so much easier to look for some kind of secret or recipe for how to live our lives and therefore how to go about our day. And I certainly I spent half a decade looking for that recipe myself, thinking that I could interview people that we're inspiring and successful and had it all together on the outside, then I could just copy paste and have the perfect day as well. But I think if there's been one sort of major lesson, it's that you can't create the same recipe when you've got different ingredients. And we just have different ingredients, like our mornings will look different depending on our various responsibilities our various energy, our our health our state of mind our commitments, our worries.

There's just so many variances as individuals. And then there's the variances of the day what might happen in the news even can affect us. And I think that to have these prescriptive, this is what a morning routine looks like, or these are the things that everybody should do before 8 AM.

It's it just it sounds ridiculous when you actually. acknowledge that each of us has a totally different life that we're dealing with. And so I think that again, it's great to take inspiration and I certainly have, and I think that's maybe what these people are offering is inspiration and tools, but it's important to remember that we can find our own way with those tools and experiment for ourselves, I think is the most.

Empowering.

Srini Rao: Hey, listener Miles here from ACAS. Thanks for listening to one of our shows. Here's a question for you. Have you ever thought about starting your own podcast? We

Madeleine Dore: believe that everybody has a

Srini Rao: story to tell. So whatever you love talking about, we know there are listeners out there who will love to hear it.

Whether you're an armchair expert or a couple of friends who love to spill the tea. Maybe you simply want to speak your mind. Start sharing your story with a podcast. With Acast, it couldn't be easier to get started. You can record and edit, grow, and make money across all listening apps, including Apple Podcasts and Spotify.

Get started with a three month free trial of our paid plan using the promo code, start. Just visit go. acast. com slash start. Acast. We're the home of podcasting.

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Yeah I think that is probably one of the reasons I liked your book so much was because there was nothing prescriptive. It wasn't like, Hey, do this and this. It was more like a philosophy of productivity book which I think was just really thoughtful and I think more than anything for me, it was like, Oh this needs to be adapted to the circumstances of your life.

But there's something that you say in this. Yeah. Oh,

Madeleine Dore: sorry. Go ahead. Oh, no. I was just going to say thank you. Sure. That means

Srini Rao: a lot. There's something you say in the book about ambition. You say alongside the pervading societal message that we are what we accomplish, we're also told we'll never be enough.

No matter how hard we work to prove our somebody ness, there's always somebody who is more of a somebody than we are. We can never be quite good enough, smart enough, successful enough, beautiful enough, fulfilled enough because there's no end point to such ambition. And this is a question that I have been wrestling with and I've been asking a lot of people and I still haven't had an answer that I'm thinking is okay, that's it.

How in the world do you find a balance between fulfillment and ambition?

Madeleine Dore: It's interesting because I'm not sure if they're on the same scale in a way, like if we're trying to find a balance, maybe they're on different totally different scales. But I think that In some ways, maybe it is about first looking at what is fulfillment?

And maybe that is the thing that's very individual. And the fact that fulfillment might not be this constant that we arrive to. And then if we acknowledge that fulfillment in and of itself might ebb and flow and change as we do across our lives, then we can see that ambition, it's. Ambition is similar in that we don't arrive anywhere for very long.

And so I think that's the tricky part of pursuing it, either maybe fulfillment or ambition. Maybe they're both the wrong goal because they're transient things. And instead it's about detaching about from landing anywhere and really just I talk about this idea of drive instead of ambition, because drive it's active and there's a sense of movement and there's not necessarily an outcome to that drive.

It's actually the driving in and of itself. It's the process essentially. Whereas we can get so caught up on the end goal of ambition or landing in fulfillment there's that whole once we arrive, it disappears. And so if we have drive that's the thing that we are in charge of that.

That's the thing that someone can't take away from us, irrespective of whether you have a bestselling book or. Something's a success or your ambitions are fulfilled or you are fulfilled. There's this drive that, that, that's the constant. And I guess maybe checking in with yourself and asking which direction is my drive in, is it in the right direction right now for where I want to go towards fulfillment?

Yeah. I don't know. It's a great question. I

Srini Rao: love that. Yeah. No it's something I've thought about. That's why I don't think I've ever found an answer yet because I don't think anybody has like a, to your point earlier, like a simple recipe for this. If it was that simple, I would have figured it out.

One thing that I really loved was the concept that you talk about called micro ambition and and then also the idea of being a time realist. And I think that we all try to squeeze in far more than we can possibly do in any given day. And that's one of the things I find with productivity apps in general, like task management tools is like the biggest sort of issue with a lot of these tools is the fact that they don't have any constraints by design.

You can just keep adding and adding. And I was like, okay, this is why I use pen and paper. But talk to me about the idea of time realism and micro ambition.

Madeleine Dore: Okay. Yeah, it's nice that you've bundled cause they're quite, they're there's a similarity, like a connection in that everything's really about taking it down to the smallest moment, isn't it? But micro ambition it's actually a concept that I've borrowed from the comedian Tim Minchin. And so he had a 2013 commencement address. Where he admits that he's never had a big dream, like a big ambition.

Instead he is an advocate for short term goals. And so the idea of being micro ambitious is that you just put your head down and work with whatever is in front of you and. The idea is that the next worthy pursuit, it's actually in the periphery. It's not on this big goal because again, if we go back to this idea of drive, the direction might change.

And so if you are open, if you're just working on this next right thing that's in front of you, it leaves you open to opportunities. It leaves you open to those possibilities. And it just means that you can actually notice what might be at the corner of your eye. interviewing people who have very successful coveted careers.

There wasn't necessarily a plan. There wasn't this step by step process. It was very much about being aware of whatever thing was out the corner of their eye and seizing different opportunities and working in the moment and not getting too caught up with where that will go. Because I think sometimes when we have this big goal, we can just focus on the gap between that big goal and where we are and get lost in that gap.

And so I think it's about trying to put that aside and just work on what's in front of you. So that's the idea of being micro ambitious and this idea of. being a time realist is I think what can get us in trouble when it comes to panicking about the time that we might waste in a day, which then leads to feelings of productivity guilt, or it might be the very thing that propels productivity obsession is because we don't want a moment of time wasted because that would be so detrimental.

But the idea is that being a time realist is that we really can crowd the day with a long to do list or we can think that we can achieve more than is actually possible in one day. So I think that links nicely to being micro ambitious because instead of crowding our to do Haha.

It's really about how can we make that smaller and more realistic and actually create buffer room and know that things actually take a lot longer than we think that they will. I think we can set ourselves up for a lot of stress just because of our expectations for how smoothly something will go.

We don't account for just distractions and disruptions. So rather than being a time optimist, it's about being a time realist and being realistic with how long things take and being okay with that space around things.

Srini Rao: Let's talk about comparison. I think that the comparison and the idea of social media go nicely together. And you talk about two types of comparison. You talk about enriching comparison and the other form of comparison, which is empty comparison. Talk to me about the distinction between the two and how you make sure that you're not falling into the trap of empty comparison.

I think that when you scroll through Instagram, you scroll through Facebook to your point you are basically getting a holographic version of somebody's life. And I've often said it's a bit like looking through a window when you walk by somebody's house and assuming that reveals everything about what their life is like.

Madeleine Dore: Yeah. When it's just a window and maybe you're even like looking at a shadow, so you don't even know. What you're really seeing, the smoke and mirrors of it all. Yeah I think that's a good way to, to summarize empty comparison in many ways is that I think that with empty comparison is that we might feel this sense of not good enough, or we might feel the sense of falling behind based on these inaccurate glimpses that we're getting of someone's life.

But not only that, but where not only what we're comparing to, could that be inaccurate? But it might actually be that we're comparing ourselves to something that we don't even actually want. If we there's been so many lessons of we might think that we should do something in a certain way or pursue a certain career because someone else did.

And because that led to success and we don't actually interrogate whether that's something we want for ourselves, whether we want to be doing those eight things before 8am. Is that something we really want for our life? So I'd say that's empty comparison is that there's no sense of real kind of congruence with what you want in your life.

Whereas enriching comparison, that's when you might encounter something. Maybe someone has just had had a glimmer of success in some way and you feel that sort of the pang of comparison. And it might feel like that envy and that jealousy or that feeling of falling behind or not good enough, it also in some ways brings you alive.

It's alerting you to something that you actually want. And it's almost providing a direction for you. And so that's enriching comparison where you can take these as a little map and there's that great Julia Cameron's book, The Artist's Way, where she advises to create a jealousy map and write down sort of the names of people of that you might be jealous of or comparing yourself to and what it is that, that they're doing that is.

It's maybe what you're coveting. And I think when I've done that exercise myself, what it's revealed to me is that I know it's enriching comparison when it's not necessarily exactly what they're doing that I want, but it's a value or an attribute. It's Oh, it's their openness. Oh, it's their courage that I'm envying.

It's, Oh they're not self conscious. It's something that's. It's more intangible and then that's what I can work with because we might not be able to do exactly what they've done in the way that they've done it. That's impossible. But we can borrow some of that inspiration and maybe some of that, those values and enrich our own lives in, in doing so through comparison.

Srini Rao: I think that dovetails nicely into the idea of expectations, because I think in a lot of ways, comparison often tends to generate expectations. And you say that we cannot rid our futures of uncertainty, but we can loosen our grip on our desire for certainty. We can change our great expectations of our future self and relieve some of the pressure.

And you say expecting so much of ourselves can curtail our ability to do something either by exacerbating our feelings of being already behind or by setting us up to fail. And I think that that really is fitting considering that you and I were both talking about our experiences with publishing books when before we hit record here and how sometimes they didn't necessarily live up to our expectations.

Like I was just telling you, I thought audience of one had been a flop commercially because it didn't hit a bestseller list or something like that. And I think that there's like a, Inherent understanding everybody has that having expectations is pretty much a recipe for disappointment.

And I have noticed in my life, anytime I have zero expectations of a situation, it usually ends up turning out far better than I ever thought it would. Anytime I have an expectation, it's almost always disappointing. And I love the way AR Rahman, the Indian composer, but he said, when you expect nothing, everything comes to you.

And I realized that's actually so hard to do. And the ultimate irony of it is to actually not have expectations when it works and you start getting all the things you wanted. That's when I realized it was actually even harder. Like the first step is easy, but when having no expectations starts to get you everything you wanted, then you start to get into this trap of, Oh, okay, now it's just going to last forever.

Madeleine Dore: Interesting. And so that, that's the part that's scary is that it's going to last forever or that it will go away, that someone will take away whatever. It is. You've always wanted.

Srini Rao: I think it'll go. Because I think the thing is that you the thing is like you detach from something, the outcome of something and suddenly the outcomes exceed whatever expectations you let go of.

And then suddenly the expectations come back now that you've got what you wanted which I think is actually the hardest thing, but I'm curious, like when you think about this idea of expectations, like how do you let go of expectations while at the same time maintaining your drive?

Madeleine Dore: I definitely don't think I've mastered letting them go entirely. So I think a little trick there is just to make them really small. And so that, I guess that's a nice tie back to micro ambition. I always think of my friend who was having a bit of a panic about a trip that she was taking abroad and this, the expectation that she has to have the trip of a lifetime and make all these memories and make the most of every.

Moment. And in that panic, she was given the advice to just go. to Europe and have a cup of coffee and then everything else can be a bonus from there. So if

,

the goal is, if the expectation is to have a coffee, it's it means that everything else can be, can be this beautiful bonus and there can be that flexibility and you can be open to different opportunities and things.

And so I think that maybe that's the way to sidestep Expectations. I think we'll always want things for ourselves. And so I guess it's about being aware of that and making them, I think there's this interesting tension between, we still want to, we still want to challenge ourselves.

And so there is something to be said for having ambition and expectation something to rise to sometimes when someone believes in us and has an expectation of us. It can be the very thing that helps us believe in ourselves and strive harder. It's just when that striving becomes relentless and that hamster wheel that can be tricky.

So I think it's always an interesting balance between accepting whatever it is but also pursuing more in where we can. Yeah. Yeah.

Srini Rao: I in a sort of ironic twist, talk to me about how you actually plan your day because I, you and I both have probably read every productivity book under the sun.

You wrote one. I've apparently filled Medium with so much productivity porn that's all I get now when I actually log in. So yeah, talk to me about how you apply this in your life day to day. What is your daily planning look like? Are you just abandon all productivity advice? I didn't get the sense that's the case.

Madeleine Dore: No, I think that it's interesting because I am still someone who is a devotee to my bullet journal, for example. And I think I will always have an affinity for a to do list. And so all of this was, there's, there can be a real joy from that. There's this sort of juicy pleasure to try in the next sort of hack.

It's just about again. Not attaching my sense of self worth to whether that changes my life or not, because chances are it's not going to change my life. I'm still the same person. And so I think that I have the list, but I hold it lightly. And instead of having this intense, elaborate schedule for myself that if it doesn't go to plan the whole day topples over, it's about okay moving on to the next thing.

Something I try to keep top of mind is this quote from Arnold Bennett who wrote a book in 1908 called How to Live on 24 Hours a Day. And he talks about how the beauty of time is it cannot be wasted in advance. And so we might waste one hour, we might waste the morning, we might've wasted the day, but we can turn over a new leaf if we choose.

And so I suppose I'm just each hour trying to turn over the new leaf and look to the next small thing that needs to be done. But recently it's this beautiful. I don't know, full circle thing where because I've really interrogated these things and tried to put away other people's recipes for the day and try to focus on what I've got to work with I found that there's this thing happening that sort of looks like a semblance of a routine I've always wanted to be.

a morning person, and I've always been someone who sets this overly ambitious alarm and then only to snooze through it because it's waking me up at a time where I'm not getting enough sleep. And so instead of trying to become this morning person through discipline and punishment, I've just allowed myself to get the sleep that I need.

And I find that I wake up at the out an earlier hour and then being able to it's really helped me see that these things that we strive for sometimes just fall into place because of the years I think that. We slowly settle into our own rhythm and get to know ourselves more and know what we need and know what feels good.

And I think exercise has been a really great example for me. It was something that I dreaded through my twenties, but now in my thirties, it's something that gives me such mental clarity that there's such delight in it that here I am with an exercise habit, but it's not through willpower. It's actually through delight.

So I think that there's just been these interesting reframes. And yeah, I think you're speaking to me at a time where I've had a very spacious purposely trying to to trim any unnecessary commitments or obligations that I'm doing out of a feeling of should, or a feeling of not falling behind or a feeling of this pressure to be busy.

And what that's meant is that I've just had more space and trying to keep the thing that I value is freedom. And so trying to keep that present. And so I guess that doesn't really answer what the day looks like, but it's an interesting like segue into what a life can look like. And I think that for me it's constantly questioning how can I have more time?

And the, I guess the trade off there is. Perhaps not pursuing material things as much. And just, yeah, I'm curious to hear about your day on the swell. The question never leaves.

Srini Rao: I'll tell you about my day, but the sort of big takeaway I think I've had from our conversation is somewhat of a paradox of productivity is the irony is the less we You know, obsessively try to be productive, the more productive we become.

And it reminds me of something Chris Bailey said in our recent interview with him about how to be calm and productive and this idea of an accomplishment mindset and how this accomplishment mindset actually pulls you out of the present moment. And as a result, actually, it's less likely to accomplish things.

And that's the big sort of takeaway, maybe the universe is trying to tell me to slow the fuck down. That's maybe the message I'm getting, considering we had Chris Bailey as the episode yesterday, and now I'm talking to you. I'm wondering, I was like, maybe the universe is trying to tell me something.

But as far as my day goes it has pretty much been standard for quite some time. One thing that did change is my sister had a baby. So now because my sister's at my parents house at least for another two weeks. He's become a, an integral part of my morning routine and we're all dreading when he's going to leave because my mom and I are like, you know what?

I think he'll adapt just fine. We're the ones who are going to have a hard time with him not being here. So like I wake up in the morning and I usually used to be 6 AM at the desk reading, writing, but since he came along cause he doesn't wake up till seven 30 and it's not like you can wake the kid up.

Like you just have to go with his schedule. He's a baby. And so I wait for him to wake up so I can hang out with him in the morning and listen to some music with him and teach him about 90s hip hop, which in my opinion is the best hip hop music ever. But it's honestly, I was thinking about this.

If there's anything that I have appreciated about him, it's that he's taught me what it means to be present. And to let go of this need to just be constantly on the ball because even my brother in law is the same thing because he has a son now it's Oh, okay.

And he's trying to balance building a startup and spending time with a kid. That's definitely changed things. But my day has always been pretty standard. Like I have, I try to have no meetings before 10 a. m. I try not to have screens in the morning. I haven't been as good about that lately because my exercise bike isn't my parents home theater.

So I just turn on something to watch cause otherwise it would be mind numbing to ride an exercise bike. But typically I usually don't spend much time on screens, at least for the first couple of hours. And then I usually am doing a lot of reading first thing in the morning. That's the bulk of my early morning is spent reading because that's when I find my mind is typically the sharpest and it tends to buy about two or 3 p.

m. decline. And I talking to is making me realize like I should just be okay with the fact that I'm going to be distracted and all over the place and chase shiny objects on the internet sometimes, which have led to some of my best ideas.

Madeleine Dore: Exactly. Yeah. The immeasurable kind of epiphanies I think that's so important and just what you're describing in terms of, I think that was really common with people I interviewed is that it's not a routine in the way that we might think of it.

It's these little anchors in the day that we've over time cultivated and know that if we do those things, it's a good day, but it might not happen every day because that's just life. And I think that the important part is just, again, picking up the pieces. And finding a way to be present in the day or enjoy the day or learn from the day.

I think that's more important than squeezing the most out of every single day because what does that even really mean? Is it squeezing the most if you got a lot of work done or is it squeezing the most if you connected with a newborn? So I I guess it's it really it's a big question I think about how, what we value.

Srini Rao: Wow. This has been beautiful and thought provoking and insightful and I have one final question for you, which I know you've heard me ask, what do you think it is that makes somebody or something unmistakable?

Madeleine Dore: I was really reflecting on this because I knew that you'd ask the question.

And. I actually, I think I landed on honesty and in particular, I think that there's some beautiful conversations around vulnerability. And I think that those conversations are really important and enriching, but I think sometimes we're actually mislabeling, we're calling things vulnerable when actually they're just honest.

And I think that there's. There's a real place for knowing what honesty looks like and recognizing it because vulnerability it's actually focusing so much on the reaction because by definition it means that you're exposed to the possibility of being attacked or harmed. And so this kind of it's what people are describing or responding to what you're doing is that thing about, Oh, you're so vulnerable.

I would never be able to do that. Or it's this warning that they're giving you Whoa, you might get hurt. Be careful. That's people's reactions. Whereas the person doing something, they might actually feel. in a creative way, really strong, really safe. They might feel like they've honed their craft.

They might feel in control of this supposedly vulnerable act, but actually what they had said, they're not being vulnerable. They're actually just being honest about something. They're being honest about a question that they've had, or they're being honest about their interpretation of something.

And so I think that can be a real beauty is this honesty that we see. And they say that the best kind of humor is actually just honesty. And I think that can be true for creativity. So when someone's honest about who they are or what they desire or they're honest about their flaws or when they say, I don't know, or I've changed my mind or I've made a mistake, those things are what we really connect to.

And I think that there's this integrity and sincerity and openness to honesty. That's unmistakable.

Srini Rao: I can't thank you enough for taking the time to join us and share your story, your wisdom and your insights with our listeners. Where can people find out more about you your work, the book and everything else you're up to?

Madeleine Dore: All of that is on MadeleineDore. com and I've got a newsletter where I continue to write about various things.

So they can also sign up and say hello there. It's also just been such a treat to be here on the Unmistakable Creative. So thank you for all the work that you do and for giving the book a chance, even though it was contrarian. I've just really appreciated the conversation.

Srini Rao: Thank you. And for everybody listening, I highly recommend that you check out this book.

I think you'll absolutely love it. And we will wrap the show with that.